Amphidinol C, a major polyketide from an Irish strain of the dinoflagellate Amphidinium carterae. (October 2022)

• Record Type: Journal Article
• Authors: Murphy, Elliot; Barone, Maria Elena; Campanile, Floriana; Touzet, Nicolas; Thomas, Olivier P.
• Is Part Of: Phytochemistry letters. Volume 51(2022)
• Page Start: 104
• Page End: 108
• Publication Date: 2022-10
• Subjects: Amphidinium carterae -- Amphidinol -- Fungicidal -- Polyketide; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2022.08.001
• Languages: English
• ISSNs: 1874-3900

Abstract

Abstract: An Irish strain of the dinoflagellate Amphidinium carterae was previously shown to produce antibacterial amphidinol derivatives of unknown masses. Inspection of the major metabolites present in a bulk culture of this strain led to the isolation and structure elucidation of a new amphidinol derivative named amphidinol C featuring an unprecedented tetrahydropyran ring between the positions C-7 and C-11. The structure was determined using extensive analyses of NMR and MS data and comparison with data of analogues. The new ring was proposed to stem from a nucleophilic substitution of the sulphate present on the side chain of Amphidinol B. The major metabolites isolated were tested for their antibacterial and antifungal activities and Amphidinol C showed moderate fungicidal activity against yeast and filamentous fungi at 8–16 µg mL −1 . Graphical Abstract: ga1 Highlights: Amphidinol C was isolated from an Irish strain of the dinoflagellate Amphidinium carterae. Amphidinol C features an unusual tetrahydropyrane ring between the positions C-7 and C-11. The tetrahydropyrane ring could result from the substitution of the sulphate group of amphidinol B. Amphidinol C exhibited moderate fungicidal activity.